CAMBRIDGE — Another landmark building in Harvard Square may soon be undergoing major changes.
Trinity Property Management, which owns The Garage, on the corner of Mt. Auburn and John F. Kennedy streets, has filed plans with the city to redevelop the funky multistory shopping center into a more modern retail and office complex.
“It’s a cool place,” said Trinity’s president, John DiGiovanni. “But it’s brutally difficult to make it work for retailers with a driveway up the middle.”
Indeed, The Garage was once a parking garage. Before that, it was the home of stables for the horse-drawn trolleys that ran between Harvard Square and downtown Boston in the late 1800s. In the 1970s, it was converted into an indoor mini-mall — all ramps and escalators — that has long housed a variety of eclectic businesses, including anime stores, the Hempest, and Cambridge’s first tattoo parlor. Today, it remains one of the few remaining pockets of Harvard Square’s weirder days.
But long before the COVID-19 pandemic, it was a struggle to draw customers off the streets to stores in the building’s cavernous inner reaches, DiGiovanni said.
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“We have seen everyone’s sales dropping for the last 10 years,” he said. “This is not new.”
The plan, of course, comes during a time of much broader change in Harvard Square, where a wave of much-loved stores and coffee shops have closed amid rent hikes and then the disappearance of students and tourists during the pandemic.
Other prominent Harvard Square buildings have changed hands in recent years. But DiGiovanni, who grew up sweeping floors in The Garage, has no plans to sell the building. Rather, his firm has spent three years studying how best to repurpose it.
Under its proposal, Trinity would add a floor to the top and convert much of the building to office space, the better to drive daytime traffic. The ground floor would stay as retail and restaurants, including a new restaurant in the huge basement space where John Harvard’s Brew House operated for a quarter-century until it closed in 2019. And there would be more windows and entryways along sections of Mt. Auburn and Dunster streets that are now largely walled-off.
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“If we liven this up I think it can be a terrific benefit for the street,” DiGiovanni said.
The extra height and square footage have already been approved in city zoning, but the plan would still need the OK of both the Cambridge Historical Commission and the Planning Board. DiGiovanni said he expects approvals to take perhaps a year, with construction lasting 18 months to two years. That would have the new Garage ready to open in 2024.
The real trick, he said, will be making sure the eclectic vibe of The Garage survives, and that it continues to help make Harvard Square a more interesting place for years to come.
“That’s kind of the forever question,” DiGiovanni said. “What’s unique about Harvard Square is just how diverse a population still uses the place. We really still have that. How do we maintain it?”
Tim Logan can be reached at timothy.logan@globe.com. Follow him @bytimlogan.